Tag Archives: Route 66 in Chicago

So – you’re off to travel Route 66 and flying into Chicago. Fantastic! Route 66 begins in the Windy City, and it is so worth spending a couple of nights here to at least see some of the sights. This is not a comprehensive guide to all that Chicago has to offer. Here’s our guide of things to do if you have 1 full day in Chicago before you hit the road:

1. Take the ‘L’ train

No trip to Chicago is complete without a ride on the iconic Elevated train. Made famous from countless movies, it’s a kind of transport unique to us Brits. It really makes you feel a part of the city, it’s a great way to get around and it’s cheap too! We loved it.

2. Eat a meal with live Jazz piano playing

This is the very piano that we listened to in the Rosebud Prime restaurant where we ate on our first night in Chicago. I’d love to say that we sought out the best jazz Chicago had to offer, but in reality we found the restaurant closest to our hotel. We were delighted that there was live music – it really made the atmosphere – even if we were a little under-dressed for the venue. The food was great (we could only afford the bar menu – tee hee), and we were treated to a monster electrical storm as we left the restaurant. It was a fab evening.

3. Have breakfast at Lou Mitchell’s

Lou Mitchell’s is on Jackson Boulevard at the original starting place of Route 66. It’s become something of a tradition for those travelling the Mother Road to start with breakfast at Lou Mitchell’s. Lou’s opened in 1923 and Route 66 opened 3 years later. They have been serving food to travellers for 90 years! We had the most amazing breakfast there – each person gets a little packet of Milk Duds and you get prunes and orange for free with your food too. We didn’t have to eat for the rest of the day. Superb.

4. Check out Union Station

The beautiful Great Hall of Chicago Union Station is well worth a visit – it really is stunning – and puts you right back into the 20s when it was built. It has featured in lots of movies – Darren’s favourite is The Untouchables, set in 1920s Chicago in the Al Capone era of the city starring Kevin Costner (that movie with the famous ‘pram down the stairway’ scene). And considering it’s a railway station, it was actually quite a peaceful place!

5. Get a photo with the Route 66 ‘Begin’ sign

This is where it all begins. Over the years, new one way systems have been introduced in Chicago, and so the original start on Jackson Boulevard has now been moved to Adams Street. You can head west from there. This picture marked the start of our adventure – it was so exciting looking up at that sign and imagining what lay between us and the end sign all the way west in California.

6. Head to Millennium Park and ‘The Bean’

This incredible sculpture nicknamed ‘The Bean’ (its official name is ‘Cloud Gate’) appears completely seamless and plays around with light, bending it this way and that and reflecting a very different view of the city back at itself. You can just about see Darren in the bottom right hand corner of the 2nd picture. Part of what I loved about Chicago is the accessibility of its art. This piece is so tactile and encourages interaction. You can walk around it and under it – you can touch it and experiment with what the different curves do to your own reflection. It’s great fun.

7. Check out the Chicago Tribune Building

This building is scattered with 149 stone fragments from other buildings from across the world that were deemed historically or politically important by the reporters who brought them back to Chicago. You can find fragments from Westminster Abbey (pictured) and the Houses of Parliament, as well as places like the Berlin Wall and President Lincoln’s home in Springfield, IL. It’s loads of fun checking out all the different buildings that are featured – and the building’s neo-gothic architecture is truly stunning.

8. Take a stroll down the Magnificent Mile

The Magnificent Mile is Chicago’s largest shopping area – but is also home to the beautiful Chicago Water Tower and some of the tallest buildings in America (such as Trump Tower). You’ll also find the Tribune Building on this stretch.

9. Rest those weary legs on the shores of Lake Michigan

By the time we made it to Lake Michigan, we were really ready for a sit down. We found a nice tree to sit under and gazed out at the huge lake that makes Chicago feel like a city by the ocean. It was very peaceful here, and the surrounding area is all parks and cycle tracks and sculptures. If it wasn’t for the skyscrapers lining the waterfront, you could be forgiven for thinking you were in a small seaside village rather than the second city in the USA.

10. Grab a coffee on Navy Pier

We were gasping for a coffee and we stopped off at Bubba Gump Shrimp on Navy Pier. The sun had started to come out by now and the humidity levels were very high. We sat inside at the bar and got quizzed on Forrest Gump by barman John (the whole place is themed on the movie – and me being a huge Forrest Gump and Tom Hanks fan, that suited just fine). It was really a fun place and the service was impeccable. Navy Pier has many other options for meals and drinks and it’s a great walk down the pier with the attractions and amusements.

11. Go up to the Skydeck in Willis Tower

The Willis Tower (formally the Sears Tower) has 3 platforms that jut out from the building over 1300ft from ground level. It really is the most peculiar feeling. I’m in no way scared of heights (this is not a thing to do if you’re scared of heights!), but my brain was shrieking at me not to step out on the ledge. A totally counter-intuitive experience, it was really quite exhilarating. I got used to it after a while, but there are plenty of photos of me gingerly stepping out onto the ledge. Well worth the time spent here – we loved it. And you get great views of Chicago!

12. See the Chicago Theatre all lit up

I just had to get a picture of the iconic Chicago Theatre at night – unfortunately, I was unwell in the evening so Darren braved the dark unknown streets (what a hero!) to get this picture. I love it.

13. Go to bed tired & happy, excited for the road ahead.

So there you have it – a whistle stop tour of Chicago in just one day – and most of it was absolutely free (there is a fee for the Willis Tower – and food always costs money of course). We had a superb day, saw many of Chicago’s highlights, and we went to bed that night tired but happy – and extremely excited about hitting the road in the morning.